(1,10-Phenanthroline)tris­(phenoxy­acetato)lanthanum(III)

Zhong, H.; Zeng, X.-R.; Yang, X.-M.; Luo, Q.-Y.; Xu, Y.-P.

doi:10.1107/S1600536807027171

Retracted: (1,10-Phenanthroline)tris(phenoxyacetato)lanthanum(III)

H. Zhong, X.-R. Zeng, X.-M. Yang, Q.-Y. Luo and Y.-P. Xu

The La^III atom in the title complex, [La(C₈H₇O₃)₃(C₁₂H₈N₂)], is coordinated by two N atoms of the 1,10-phenanthroline ligand and four O atoms of three phenoxyacetate ligands. This mononuclear complex is further extended into a supramolecular network structure via nonclassical hydrogen bonds between CH groups of 1,10-phenanthroline and phenoxyacetate and O atoms of neighbouring phenoxyacetate ligands.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027171/bq2017sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027171/bq2017Isup2.hkl Contains datablock I

CCDC reference: 1148881

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.009 Å
R factor = 0.036
wR factor = 0.090
Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.43
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.83 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C25
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C31
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         O9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      74.00 A   3 

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for La1         (3)       3.37
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

In recent years, there has been great interest in the synthesis of metal organic frameworks (MOFs) with organic ligands and rare earth metals because of their novel structures, fascinating properties and important roles in special materials having optical, electronic, magnetic and biological importance potential applications (Deborah et al., 2000; Farrugia et al., 2000; Tsukube & Shinoda, 2002; Zhang et al., 2005). These compounds are usually prepared by the reaction of rare-earth metal ions with bi- or multidentate ligands (Starynowicz, 1991, 1993; Kay et al., 1972; Ma et al., 1999; Zeng et al., 2000; Mao et al., 1998).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The six-coordinate environment of the La atom is completed by the two N atoms of 1,10-phenanthroline ligand and four O atoms of three phenoxyacetic acid ligands (Table 1). The La—O bond lengths are in the range 2.4175 (19) to 2.827 (2) Å. The La—N bond lengths are in the range 2.707 (2) to 2.750 (3) Å. C—H···O non-classica hydrogen bonds between C—H groups of 1,10-phenanthroline or phenoxyacetic acid and O atoms of neighbouring phenoxyacetic acid molecules, with an average C···O distances of 3.179 (9) Å, generate a layered hydrogen-bonded network (Fig. 2 and Table 2). The non-classical hydrogen-bonding interactions link the mononuclear complex into a supramolecular network structure.

Related literature top

For related literature, see: Allen et al. (1987); Farrugia et al. (2000); Kay et al. (1972); Ma et al. (1999); Mao et al. (1998); Starynowicz (1991, 1993); Tsukube & Shinoda (2002); Zhang et al. (2005); Zeng et al. (2000).

Experimental top

Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb, which was then sealed. Lanthanum (III) chloride hexahydrate (70.7 mg, 0.2 mmol), phen (39.6 mg, 0.2 mmol), phenoxyacetic acid (91.3 mg, 0.6 mmol) and distilled water (4 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure up to 413 K over the course of 7 d and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colorless solution was decanted from small colorless crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. View of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. All H atoms have been omitted for clarity.
	Fig. 2. A packing diagram of (I) wieved down to b axis. Hydrogen bonds are shown as dashed lines. Part H atoms have been omitted for clarity. [Symmetry code: (A) 2 - x, -y, 2 - z; (B) 1 - x, 1 - y, 1 - z; (C) x - 1, 1/2 - y, z - 1/2; (D) 1 - x, 1/2 + y, 3/2 - z; (E) x, y, z; (F) 2 - x, 1 - y, 2 - z]

(1,10-Phenanthroline)tris(phenoxyacetato)lanthanum(III) top

Crystal data top

[La(C₈H₇O₃)₃(C₁₂H₈N₂)]	F(000) = 1552
M_r = 772.52	D_x = 1.502 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9081 reflections
a = 20.182 (3) Å	θ = 2.5–27.0°
b = 8.5307 (11) Å	µ = 1.31 mm⁻¹
c = 20.833 (3) Å	T = 273 K
β = 107.779 (2)°	Plane, colorless
V = 3415.5 (8) Å³	0.33 × 0.12 × 0.08 mm
Z = 4

Data collection top

Bruker APEX II area-detector diffractometer	6634 independent reflections
Radiation source: fine-focus sealed tube	4671 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
φ and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→24
T_min = 0.674, T_max = 0.903	k = −10→10
24692 measured reflections	l = −25→25

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0436P)² + 0.615P] where P = (F_o² + 2F_c²)/3
6634 reflections	(Δ/σ)_max = 0.001
403 parameters	Δρ_max = 1.43 e Å⁻³
3 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[La(C₈H₇O₃)₃(C₁₂H₈N₂)]	V = 3415.5 (8) Å³
M_r = 772.52	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 20.182 (3) Å	µ = 1.31 mm⁻¹
b = 8.5307 (11) Å	T = 273 K
c = 20.833 (3) Å	0.33 × 0.12 × 0.08 mm
β = 107.779 (2)°

Data collection top

Bruker APEX II area-detector diffractometer	6634 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4671 reflections with I > 2σ(I)
T_min = 0.674, T_max = 0.903	R_int = 0.040
24692 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	3 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.07	Δρ_max = 1.43 e Å⁻³
6634 reflections	Δρ_min = −0.59 e Å⁻³
403 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
La1	0.931205 (11)	0.19064 (2)	0.964291 (10)	0.03933 (9)
O1	0.97062 (14)	0.0601 (3)	0.87477 (12)	0.0530 (7)
O2	1.06694 (14)	−0.0829 (3)	0.92161 (13)	0.0557 (7)
O3	1.11837 (16)	−0.0162 (4)	0.82201 (15)	0.0735 (9)
O4	0.94007 (14)	0.4209 (3)	1.03406 (12)	0.0535 (7)
O5	1.00792 (16)	0.6128 (3)	1.09095 (13)	0.0635 (8)
O6	0.98698 (16)	0.5279 (3)	1.20623 (13)	0.0681 (9)
O7	0.84638 (13)	−0.0360 (3)	0.91880 (13)	0.0505 (7)
O8	0.94658 (13)	−0.1382 (4)	0.97709 (13)	0.0555 (7)
O9	0.78443 (16)	−0.3265 (3)	0.89809 (16)	0.0696 (9)
N1	0.79701 (17)	0.2347 (4)	0.96669 (17)	0.0533 (8)
N2	0.83407 (18)	0.3069 (4)	0.85438 (16)	0.0535 (8)
C1	0.7780 (2)	0.1918 (5)	1.0201 (2)	0.0688 (13)
H1	0.8127	0.1685	1.0600	0.083*
C2	0.7092 (3)	0.1804 (7)	1.0191 (3)	0.0892 (17)
H2	0.6984	0.1506	1.0577	0.107*
C3	0.6582 (3)	0.2128 (7)	0.9617 (4)	0.099 (2)
H3	0.6119	0.2044	0.9605	0.119*
C4	0.6745 (3)	0.2591 (7)	0.9041 (3)	0.0810 (16)
C5	0.7460 (2)	0.2676 (5)	0.9087 (2)	0.0573 (11)
C6	0.6233 (3)	0.2982 (8)	0.8400 (4)	0.116 (2)
H6	0.5762	0.2901	0.8357	0.139*
C7	0.6424 (3)	0.3453 (8)	0.7875 (3)	0.109 (2)
H7	0.6084	0.3728	0.7478	0.131*
C8	0.7134 (3)	0.3547 (6)	0.7905 (2)	0.0764 (15)
C9	0.7659 (2)	0.3100 (5)	0.8504 (2)	0.0571 (11)
C10	0.7354 (4)	0.4029 (7)	0.7366 (3)	0.0936 (19)
H10	0.7028	0.4371	0.6971	0.112*
C11	0.8036 (3)	0.4011 (6)	0.7406 (2)	0.0872 (17)
H11	0.8179	0.4335	0.7043	0.105*
C12	0.8526 (3)	0.3489 (5)	0.8009 (2)	0.0692 (13)
H12	0.8993	0.3438	0.8033	0.083*
C13	1.0287 (2)	0.0035 (5)	0.87698 (19)	0.0473 (9)
C14	1.0525 (2)	0.0507 (5)	0.8173 (2)	0.0608 (11)
H14A	1.0185	0.0161	0.7759	0.073*
H14B	1.0557	0.1640	0.8157	0.073*
C15	1.1456 (3)	0.0146 (6)	0.7704 (2)	0.0679 (13)
C16	1.2080 (3)	−0.0552 (7)	0.7767 (3)	0.0873 (16)
H16	1.2293	−0.1162	0.8144	0.105*
C17	1.2400 (3)	−0.0352 (8)	0.7268 (4)	0.1020 (19)
H17	1.2824	−0.0835	0.7309	0.122*
C18	1.2094 (4)	0.0543 (8)	0.6722 (4)	0.110 (2)
H18	1.2307	0.0669	0.6387	0.132*
C19	1.1481 (4)	0.1252 (8)	0.6664 (3)	0.113 (2)
H19	1.1277	0.1876	0.6289	0.136*
C20	1.1149 (3)	0.1063 (7)	0.7158 (3)	0.0902 (17)
H20	1.0726	0.1553	0.7114	0.108*
C21	0.9692 (2)	0.4993 (5)	1.08630 (19)	0.0490 (10)
C22	0.9490 (2)	0.4462 (5)	1.14728 (19)	0.0618 (11)
H22A	0.8996	0.4638	1.1391	0.074*
H22B	0.9577	0.3346	1.1540	0.074*
C23	0.9748 (2)	0.4889 (5)	1.2657 (2)	0.0598 (11)
C24	0.9277 (3)	0.3797 (7)	1.2719 (2)	0.0801 (15)
H24	0.9014	0.3240	1.2345	0.096*
C25	0.9197 (4)	0.3526 (9)	1.3349 (3)	0.113 (2)
H25	0.8883	0.2768	1.3394	0.136*
C26	0.9566 (4)	0.4343 (9)	1.3897 (3)	0.110 (2)
H26	0.9496	0.4173	1.4312	0.132*
C27	1.0043 (3)	0.5416 (7)	1.3837 (2)	0.0969 (18)
H27	1.0305	0.5964	1.4215	0.116*
C28	1.0142 (3)	0.5702 (6)	1.3219 (2)	0.0778 (14)
H28	1.0471	0.6432	1.3181	0.093*
C29	0.8843 (2)	−0.1515 (5)	0.93930 (19)	0.0489 (10)
C30	0.8575 (2)	−0.3151 (5)	0.9191 (2)	0.0610 (11)
H30A	0.8745	−0.3503	0.8827	0.073*
H30B	0.8763	−0.3849	0.9571	0.073*
C31	0.7516 (5)	−0.3130 (8)	0.9450 (5)	0.1338 (13)
C32	0.7850 (5)	−0.2767 (8)	1.0120 (5)	0.1338 (13)
H32	0.8329	−0.2613	1.0275	0.161*
C33	0.7437 (4)	−0.2637 (8)	1.0562 (5)	0.1338 (13)
H33	0.7638	−0.2385	1.1015	0.161*
C34	0.6746 (5)	−0.2888 (8)	1.0310 (5)	0.1338 (13)
H34	0.6477	−0.2755	1.0598	0.161*
C35	0.6406 (5)	−0.3336 (8)	0.9643 (5)	0.1338 (13)
H35	0.5936	−0.3594	0.9501	0.161*
C36	0.6801 (4)	−0.3378 (8)	0.9205 (4)	0.1338 (13)
H36	0.6589	−0.3572	0.8749	0.161*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
La1	0.04562 (13)	0.03362 (13)	0.03345 (12)	−0.00164 (10)	0.00420 (8)	0.00052 (10)
O1	0.0624 (17)	0.0522 (17)	0.0435 (15)	0.0088 (15)	0.0148 (13)	0.0025 (13)
O2	0.0667 (17)	0.0541 (18)	0.0462 (16)	0.0083 (15)	0.0173 (13)	0.0111 (14)
O3	0.074 (2)	0.091 (2)	0.0632 (19)	0.0191 (18)	0.0323 (16)	0.0229 (17)
O4	0.0757 (18)	0.0386 (16)	0.0436 (15)	−0.0067 (14)	0.0140 (13)	−0.0063 (13)
O5	0.092 (2)	0.0529 (19)	0.0445 (16)	−0.0291 (17)	0.0192 (15)	−0.0019 (13)
O6	0.096 (2)	0.066 (2)	0.0420 (16)	−0.0290 (17)	0.0206 (15)	−0.0074 (14)
O7	0.0510 (15)	0.0388 (16)	0.0524 (16)	0.0003 (13)	0.0021 (12)	−0.0032 (12)
O8	0.0492 (16)	0.0594 (18)	0.0477 (16)	−0.0039 (13)	−0.0005 (13)	0.0073 (13)
O9	0.065 (2)	0.050 (2)	0.078 (2)	−0.0146 (15)	−0.0026 (16)	−0.0072 (16)
N1	0.053 (2)	0.047 (2)	0.051 (2)	0.0039 (16)	0.0044 (17)	−0.0078 (16)
N2	0.067 (2)	0.040 (2)	0.0426 (19)	0.0027 (17)	0.0014 (16)	0.0006 (15)
C1	0.063 (3)	0.083 (4)	0.059 (3)	0.008 (3)	0.017 (2)	−0.002 (3)
C2	0.061 (3)	0.126 (5)	0.085 (4)	0.005 (3)	0.030 (3)	−0.015 (3)
C3	0.054 (3)	0.120 (6)	0.119 (5)	−0.003 (3)	0.020 (3)	−0.019 (4)
C4	0.053 (3)	0.091 (4)	0.082 (4)	0.008 (3)	−0.005 (3)	−0.021 (3)
C5	0.054 (3)	0.043 (3)	0.065 (3)	0.0060 (19)	0.003 (2)	−0.011 (2)
C6	0.063 (4)	0.147 (7)	0.111 (5)	0.014 (4)	−0.014 (4)	−0.028 (5)
C7	0.081 (4)	0.120 (6)	0.089 (5)	0.038 (4)	−0.030 (3)	−0.015 (4)
C8	0.081 (4)	0.066 (3)	0.057 (3)	0.018 (3)	−0.016 (3)	−0.009 (2)
C9	0.062 (3)	0.040 (2)	0.051 (2)	0.005 (2)	−0.011 (2)	−0.005 (2)
C10	0.119 (5)	0.076 (4)	0.053 (3)	0.019 (4)	−0.022 (3)	0.001 (3)
C11	0.125 (5)	0.076 (4)	0.044 (3)	−0.002 (4)	0.001 (3)	0.011 (3)
C12	0.090 (3)	0.058 (3)	0.050 (3)	−0.003 (2)	0.006 (2)	0.008 (2)
C13	0.061 (3)	0.037 (2)	0.042 (2)	−0.004 (2)	0.0124 (19)	−0.0016 (17)
C14	0.070 (3)	0.061 (3)	0.054 (3)	0.007 (2)	0.022 (2)	0.012 (2)
C15	0.076 (3)	0.073 (3)	0.065 (3)	−0.006 (3)	0.037 (3)	0.001 (2)
C16	0.086 (4)	0.107 (5)	0.081 (4)	0.002 (3)	0.043 (3)	0.001 (3)
C17	0.098 (4)	0.107 (5)	0.123 (5)	−0.006 (4)	0.066 (4)	−0.008 (4)
C18	0.148 (6)	0.090 (5)	0.126 (6)	−0.017 (5)	0.095 (5)	0.000 (4)
C19	0.159 (6)	0.108 (5)	0.101 (5)	0.016 (5)	0.082 (5)	0.031 (4)
C20	0.109 (4)	0.097 (4)	0.082 (4)	0.010 (4)	0.056 (3)	0.026 (3)
C21	0.064 (3)	0.038 (2)	0.043 (2)	−0.002 (2)	0.0134 (19)	0.0020 (18)
C22	0.080 (3)	0.059 (3)	0.047 (2)	−0.020 (2)	0.020 (2)	−0.006 (2)
C23	0.077 (3)	0.060 (3)	0.042 (2)	−0.003 (2)	0.017 (2)	0.003 (2)
C24	0.088 (4)	0.096 (4)	0.060 (3)	−0.034 (3)	0.027 (3)	−0.003 (3)
C25	0.133 (5)	0.148 (6)	0.070 (4)	−0.062 (5)	0.047 (4)	−0.002 (4)
C26	0.138 (5)	0.144 (6)	0.055 (3)	−0.030 (5)	0.042 (3)	0.008 (4)
C27	0.125 (5)	0.113 (5)	0.045 (3)	−0.022 (4)	0.015 (3)	−0.009 (3)
C28	0.095 (4)	0.081 (4)	0.053 (3)	−0.022 (3)	0.017 (2)	−0.010 (3)
C29	0.053 (2)	0.052 (3)	0.037 (2)	−0.004 (2)	0.0066 (18)	−0.0027 (18)
C30	0.066 (3)	0.047 (3)	0.061 (3)	0.003 (2)	0.007 (2)	−0.006 (2)
C31	0.148 (3)	0.098 (2)	0.182 (4)	0.017 (2)	0.089 (3)	0.031 (2)
C32	0.148 (3)	0.098 (2)	0.182 (4)	0.017 (2)	0.089 (3)	0.031 (2)
C33	0.148 (3)	0.098 (2)	0.182 (4)	0.017 (2)	0.089 (3)	0.031 (2)
C34	0.148 (3)	0.098 (2)	0.182 (4)	0.017 (2)	0.089 (3)	0.031 (2)
C35	0.148 (3)	0.098 (2)	0.182 (4)	0.017 (2)	0.089 (3)	0.031 (2)
C36	0.148 (3)	0.098 (2)	0.182 (4)	0.017 (2)	0.089 (3)	0.031 (2)

Geometric parameters (Å, º) top

La1—O1	2.501 (3)	C11—C12	1.413 (6)
La1—O4	2.417 (3)	C11—H11	0.9300
La1—O7	2.564 (2)	C12—H12	0.9300
La1—O8	2.826 (3)	C13—C14	1.518 (5)
La1—N1	2.750 (3)	C14—H14A	0.9700
La1—N2	2.707 (3)	C14—H14B	0.9700
La1—O8ⁱ	2.436 (3)	C15—C16	1.362 (7)
La1—O2ⁱ	2.538 (2)	C15—C20	1.363 (7)
La1—O5ⁱⁱ	2.551 (3)	C16—C17	1.392 (7)
O1—C13	1.255 (4)	C16—H16	0.9300
O2—C13	1.251 (4)	C17—C18	1.351 (8)
O2—La1ⁱ	2.538 (2)	C17—H17	0.9300
O3—C15	1.375 (5)	C18—C19	1.349 (8)
O3—C14	1.422 (5)	C18—H18	0.9300
O4—C21	1.259 (4)	C19—C20	1.398 (7)
O5—C21	1.230 (5)	C19—H19	0.9300
O5—La1ⁱⁱ	2.551 (3)	C20—H20	0.9300
O6—C23	1.376 (5)	C21—C22	1.517 (5)
O6—C22	1.417 (4)	C22—H22A	0.9700
O7—C29	1.241 (5)	C22—H22B	0.9700
O8—C29	1.268 (5)	C23—C24	1.365 (6)
O8—La1ⁱ	2.436 (3)	C23—C28	1.383 (6)
O9—C31	1.343 (8)	C24—C25	1.390 (7)
O9—C30	1.408 (5)	C24—H24	0.9300
N1—C1	1.334 (5)	C25—C26	1.350 (8)
N1—C5	1.356 (5)	C25—H25	0.9300
N2—C12	1.327 (5)	C26—C27	1.362 (8)
N2—C9	1.354 (5)	C26—H26	0.9300
C1—C2	1.386 (6)	C27—C28	1.383 (7)
C1—H1	0.9300	C27—H27	0.9300
C2—C3	1.347 (8)	C28—H28	0.9300
C2—H2	0.9300	C29—C30	1.509 (5)
C3—C4	1.396 (8)	C30—H30A	0.9700
C3—H3	0.9300	C30—H30B	0.9700
C4—C5	1.418 (6)	C31—C32	1.387 (11)
C4—C6	1.457 (8)	C31—C36	1.392 (11)
C5—C9	1.436 (6)	C32—C33	1.425 (9)
C6—C7	1.328 (9)	C32—H32	0.9300
C6—H6	0.9300	C33—C34	1.347 (10)
C7—C8	1.418 (8)	C33—H33	0.9300
C7—H7	0.9300	C34—C35	1.402 (11)
C8—C10	1.390 (8)	C34—H34	0.9300
C8—C9	1.420 (6)	C35—C36	1.383 (9)
C10—C11	1.353 (7)	C35—H35	0.9300
C10—H10	0.9300	C36—H36	0.9300

O1—La1—O4	145.89 (9)	C12—C11—H11	120.7
O1—La1—O7	73.58 (9)	N2—C12—C11	122.1 (5)
O1—La1—O8	65.02 (8)	N2—C12—H12	118.9
O4—La1—O7	138.87 (9)	C11—C12—H12	118.9
O4—La1—O8	139.82 (8)	O2—C13—O1	127.7 (4)
O7—La1—O8	47.79 (7)	O2—C13—C14	119.2 (4)
O1—La1—N1	127.85 (9)	O1—C13—C14	113.1 (3)
O4—La1—N1	76.73 (9)	O3—C14—C13	111.1 (3)
O7—La1—N1	63.87 (9)	O3—C14—H14A	109.4
O8—La1—N1	102.38 (9)	C13—C14—H14A	109.4
O1—La1—N2	81.11 (9)	O3—C14—H14B	109.4
O4—La1—N2	96.46 (9)	C13—C14—H14B	109.4
O7—La1—N2	74.58 (9)	H14A—C14—H14B	108.0
O8—La1—N2	118.27 (8)	C16—C15—C20	120.2 (5)
N1—La1—N2	60.16 (11)	C16—C15—O3	114.8 (4)
O4—La1—O8ⁱ	88.28 (10)	C20—C15—O3	125.0 (4)
O8ⁱ—La1—O1	77.78 (9)	C15—C16—C17	119.9 (6)
O4—La1—O2ⁱ	75.76 (9)	C15—C16—H16	120.0
O8ⁱ—La1—O2ⁱ	74.99 (9)	C17—C16—H16	120.0
O1—La1—O2ⁱ	128.31 (9)	C18—C17—C16	120.1 (6)
O4—La1—O5ⁱⁱ	77.28 (9)	C18—C17—H17	120.0
O8ⁱ—La1—O5ⁱⁱ	78.07 (10)	C16—C17—H17	120.0
O1—La1—O5ⁱⁱ	69.48 (9)	C19—C18—C17	120.0 (6)
O2ⁱ—La1—O5ⁱⁱ	142.10 (9)	C19—C18—H18	120.0
O8ⁱ—La1—O7	120.43 (9)	C17—C18—H18	120.0
O2ⁱ—La1—O7	83.70 (9)	C18—C19—C20	120.9 (6)
O5ⁱⁱ—La1—O7	133.46 (8)	C18—C19—H19	119.5
O8ⁱ—La1—N2	148.44 (10)	C20—C19—H19	119.5
O2ⁱ—La1—N2	136.43 (10)	C15—C20—C19	118.9 (6)
O5ⁱⁱ—La1—N2	72.66 (10)	C15—C20—H20	120.6
O8ⁱ—La1—N1	150.22 (10)	C19—C20—H20	120.6
O2ⁱ—La1—N1	76.43 (9)	O5—C21—O4	127.2 (4)
O5ⁱⁱ—La1—N1	122.08 (10)	O5—C21—C22	119.7 (4)
O8ⁱ—La1—O8	72.87 (10)	O4—C21—C22	113.0 (4)
O2ⁱ—La1—O8	65.31 (8)	O6—C22—C21	111.5 (3)
O5ⁱⁱ—La1—O8	129.85 (9)	O6—C22—H22A	109.3
C13—O1—La1	130.5 (2)	C21—C22—H22A	109.3
C13—O2—La1ⁱ	137.6 (3)	O6—C22—H22B	109.3
C15—O3—C14	117.3 (3)	C21—C22—H22B	109.3
C21—O4—La1	151.7 (3)	H22A—C22—H22B	108.0
C21—O5—La1ⁱⁱ	149.8 (3)	C24—C23—O6	124.8 (4)
C23—O6—C22	117.6 (3)	C24—C23—C28	119.9 (4)
C29—O7—La1	101.5 (2)	O6—C23—C28	115.2 (4)
C29—O8—La1ⁱ	162.7 (3)	C23—C24—C25	119.2 (5)
C29—O8—La1	88.3 (2)	C23—C24—H24	120.4
La1ⁱ—O8—La1	107.13 (10)	C25—C24—H24	120.4
C31—O9—C30	118.1 (5)	C26—C25—C24	121.2 (5)
C1—N1—C5	117.8 (4)	C26—C25—H25	119.4
C1—N1—La1	120.9 (3)	C24—C25—H25	119.4
C5—N1—La1	119.8 (3)	C25—C26—C27	119.6 (5)
C12—N2—C9	119.0 (4)	C25—C26—H26	120.2
C12—N2—La1	119.5 (3)	C27—C26—H26	120.2
C9—N2—La1	121.3 (3)	C26—C27—C28	120.7 (5)
N1—C1—C2	123.3 (5)	C26—C27—H27	119.6
N1—C1—H1	118.4	C28—C27—H27	119.6
C2—C1—H1	118.4	C23—C28—C27	119.3 (5)
C3—C2—C1	119.4 (5)	C23—C28—H28	120.4
C3—C2—H2	120.3	C27—C28—H28	120.4
C1—C2—H2	120.3	O7—C29—O8	122.2 (4)
C2—C3—C4	120.3 (5)	O7—C29—C30	120.5 (4)
C2—C3—H3	119.9	O8—C29—C30	117.3 (4)
C4—C3—H3	119.9	O9—C30—C29	113.8 (3)
C3—C4—C5	117.3 (5)	O9—C30—H30A	108.8
C3—C4—C6	124.5 (6)	C29—C30—H30A	108.8
C5—C4—C6	118.2 (6)	O9—C30—H30B	108.8
N1—C5—C4	122.0 (5)	C29—C30—H30B	108.8
N1—C5—C9	118.2 (4)	H30A—C30—H30B	107.7
C4—C5—C9	119.8 (4)	O9—C31—C32	123.7 (8)
C7—C6—C4	121.5 (6)	O9—C31—C36	114.0 (9)
C7—C6—H6	119.3	C32—C31—C36	122.3 (8)
C4—C6—H6	119.3	C31—C32—C33	117.9 (9)
C6—C7—C8	121.6 (5)	C31—C32—H32	121.1
C6—C7—H7	119.2	C33—C32—H32	121.1
C8—C7—H7	119.2	C34—C33—C32	118.4 (9)
C10—C8—C7	123.3 (5)	C34—C33—H33	120.8
C10—C8—C9	117.0 (5)	C32—C33—H33	120.8
C7—C8—C9	119.7 (5)	C33—C34—C35	124.4 (8)
N2—C9—C8	122.0 (4)	C33—C34—H34	117.8
N2—C9—C5	119.0 (3)	C35—C34—H34	117.8
C8—C9—C5	119.0 (5)	C36—C35—C34	117.0 (9)
C11—C10—C8	121.1 (5)	C36—C35—H35	121.5
C11—C10—H10	119.4	C34—C35—H35	121.5
C8—C10—H10	119.4	C35—C36—C31	119.7 (9)
C10—C11—C12	118.7 (5)	C35—C36—H36	120.1
C10—C11—H11	120.7	C31—C36—H36	120.1

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O7ⁱⁱⁱ	0.93	2.33	3.196 (5)	156
C30—H30B···O4^iv	0.97	2.39	3.339 (5)	166
C12—H12···O5ⁱⁱ	0.93	2.45	3.039 (5)	122
C1—H1···O2ⁱ	0.93	2.45	3.132 (5)	130

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[La(C₈H₇O₃)₃(C₁₂H₈N₂)]
M_r	772.52
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	20.182 (3), 8.5307 (11), 20.833 (3)
β (°)	107.779 (2)
V (Å³)	3415.5 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.31
Crystal size (mm)	0.33 × 0.12 × 0.08

Data collection
Diffractometer	Bruker APEX II area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.674, 0.903
No. of measured, independent and observed [I > 2σ(I)] reflections	24692, 6634, 4671
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.090, 1.07
No. of reflections	6634
No. of parameters	403
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.43, −0.59

Computer programs: APEX2 (Bruker, 2004), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996), SHELXTL.

Selected bond lengths (Å) top

La1—O1	2.501 (3)	La1—O8	2.826 (3)
La1—O4	2.417 (3)	La1—N1	2.750 (3)
La1—O7	2.564 (2)	La1—N2	2.707 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O7ⁱ	0.93	2.33	3.196 (5)	156
C30—H30B···O4ⁱⁱ	0.97	2.39	3.339 (5)	166
C12—H12···O5ⁱⁱⁱ	0.93	2.45	3.039 (5)	122
C1—H1···O2^iv	0.93	2.45	3.132 (5)	130

Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) x, y−1, z; (iii) −x+2, −y+1, −z+2; (iv) −x+2, −y, −z+2.

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Retracted: (1,10-Phenanthroline)tris­(phenoxy­acetato)lanthanum(III)

Supporting information

Key indicators

checkCIF/PLATON results

Retracted: (1,10-Phenanthroline)tris(phenoxyacetato)lanthanum(III)